


Dizzy with a Dame

by LostImmortality



Category: Undertale (Video Game)
Genre: Arranged Marriage, F/M, Horrormafia, Monsters are on the surface, Reader is involved in the mafia, Slow Burn, This is some kind of strange amalgamation between Mafiatale and Horrortale, Violence, probabably guns
Language: English
Status: In-Progress
Published: 2018-09-27
Updated: 2018-10-04
Packaged: 2019-07-18 09:38:46
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 4,617
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16115756
Author URL: https://archiveofourown.org/users/LostImmortality/pseuds/LostImmortality
Summary: It’s not really surprising to anyone when the city is inevitably taken over by the new monster mafia groups. It is surprising, however, when one of said mafia groups reaches out to one of the last human groups that still remain in the city.What could they possibly want?





	1. A Relutant Agreement

The sound of the front door slamming echoed through the house, easily reaching the kitchen. It was followed by a familiar set of footsteps getting closer. You didn’t bother in stopping what you were doing, already knowing who it was.

Your father stuck his head in the doorway. He gave you a small smile once he saw you plating the food you had been cooking.

“Ah! Just in time for lunch,” he grabbed the plate that you had been holding, and began towards the dining room. You grabbed your own food and followed him out.

“How was your meeting?” You asked impatiently. He had been gone all morning, having been called on by someone that you had never expected. Naturally, he agreed to go in hopes of establishing some kind of peace. You had been waiting anxiously for him to get home for a couple of hours.

Historically, it wasn’t often that meetings were requested between humans and monsters. Even less so if it was from the one that no one knew anything about, and it was under the pretense of an agreement of sorts.

Monsters had been on the surface for a few years, and the life in Ebott city had changed drastically since then. In fact, it wasn’t long before monsters had taken over the entire city, their two rival gangs ruling out whatever had already been there. You were very lucky to have avoided the entire mess that had happened in the first few months of the monsters resurfacing. In fact, you and your whole ‘family’ were lucky to be alive.

There were, of course, a few human mobs that still stood opposing them. They were there long before the monsters showed up, and you knew that they would be damned to give up their control over the city without fighting tooth and nail for it. You really hoped that it never went quite that far though. You were perfectly content with the tense silent dislike that came from all sides.

Monsters were dangerous. You knew that for a fact. You had no idea if it had always been that way, but thousands of years trapped underneath a mountain hadn’t treated them kindly. You were just lucky that the amounts of run-ins you had with them was low.

Avoiding them completely was impossible, though. Especially considering that the occupation of your father put him, and you by extension, directly on their radar. Growing up with it, you had become pretty accustomed to being in constant danger, and looking over your shoulder had become a second nature. That hadn’t steered you wrong so far, and you were willing to bet that it would continue to do you good.

“About that,” your father began, rubbing at the back of his neck, “I met with the head of the Aster family.”

You shook your head, “Yes, you told me that. But what did he want? I highly doubt that another mob boss called you to a meeting for tea.”

He stared at you for a moment, seemingly contemplating something. Then, he looked away with a small head shake, “No, you’re right. He wanted to make an… alliance of sorts with us.”

“Really?” You weren’t sure if had asked that in disbelief or surprise.

“Yes, but there was a condition.” He still refused to meet your gaze. That made you nervous. Did you really want to know what the condition was? Yes, you decided without much thought. It had to be important.

“What did he want?” You crossed your arms as you waited for him to answer.

“He wanted a collateral of sorts.”

“Of sorts?” You were beginning to get a bit uncomfortable with the way he was skirting around what was asked of him.

He grimaced at you, “I’m sorry. You aren’t going to like it, but I thought it was best.”

“What did you do? What did you promise him?” Now you were worried. It was very out of character for your father to hide things from you, especially things like this.

“Before I tell you, I need you to understand that this may have been the only chance to make peace with them. You know how dangerous they can be, and having them on our side would be better than the alternative.”

“I understand. I know that whatever you did was what you thought was best,” you gave him a nod. Though he was making it out to be like he had done something unforgivable, you knew that your father would never do anything to hurt his family.

“He wanted you.” You flinched back at his words, but he continued before you could ask him to elaborate, “Wait, that’s not right. Let me try that again. He offered an alliance, and as a collateral, he wants you to, well,” he trailed off before taking a breath, “He wants you to marry his son.”

Your eyes widened as you stared at him in a stunned silence. Eventually your surprise melted away into a flood of emotions that you couldn’t quite puzzle together.

“Please tell me you didn’t,” you sunk into your seat. A grimace fell on your face as you pleaded with him. You didn’t really have anything against human-monster relationships, but you didn’t want to be forced into one!

“I know, I know. I’m sorry. We arranged an event for the two of you. If you really still don’t want to do it after that, I’ll… I’ll see what I can do.”

“An _event_ ?” You stood up from your seat, the sound of the chair screeching against the floor as you glared at him, “Are you _kidding me_ ? This isn’t the seventeenth century, and I’m _not_ some kind of mail order bride!” You slammed your hands on the table in frustration, “You know that I won’t do anything to stop it, because I don’t want to be the reason everyone dies! You can’t just promise me to someone and go back on your word like that! It’ll start a full on war! You- you- I-“ You fell back into your seat with a frustrated growl.

“I would rather you be married to someone you don’t like than dead.” He stood up, “I know it’s unfair, and I’m _sorry_. There wasn’t any other way. I tried, I looked for one!”

You felt your anger ebb away, “I-“ you trailed off.

You knew that he just wanted what was best for you, and what was best for the rest of the ‘family’. Monsters were undoubtedly the biggest threat to all of you, and eliminating the threat of at least one of their mafias would make everything so much easier for everyone involved. And, well, you had to admit that marriage was both the easiest and most sure way to let that happen. You understood why he did that, and you were angry about that.

You dropped your head into your hands and sighed, “Alright.”

“Alright?” He asked, sitting back down as well, “You don’t have to like him. You don’t even have to be around him if you don’t want to.”

You knew he was trying to help, but that just made you feel worse. You didn’t want to marry someone you hated.

But, maybe you wouldn’t. Maybe it wouldn’t be as miserable as you were thinking it would be. If you had to do it, you were going to try to make the best out of a bad situation. You couldn’t just assume the worst of… whoever it was that you were marrying. You could at least extend that courtesy. There was a very good chance that he was about as thrilled with the idea as you were, which was to say, not at all.

You were just going to have to grin and bare it, no matter how much you wished that you didn’t have to.

**Notes for the Chapter:**

> This is a very short first chapter that kind of just... drops ya right on into it. Sorry about that!
> 
> Hope you guys like this story! I have no clue where I’m going with it, but I’m excited about it anyways!


	2. Behind the Eight Ball

**Summary for the Chapter:**

> An entire ball? Just for you??

“I can’t believe that you guys decided to arrange an entire ball,” you pointed out, fiddling with the clasp on your necklace. 

“It was mostly his doing,” your father explained reaching over to help you fasten it. You dropped your hands and let him, giving him a nod in appreciation. 

“I figured. I know how much you hate these kinds of things,” you smiled, “You always send me instead.”

“Yes, well, you’re much more charming than I am.” He took a step back and began heading outside now that the two of you were ready. You followed right behind him.

“You’re too harsh on yourself. I think you’d be plenty charming,” you pulled the car door open and glanced at him over the car with a cheeky smile, “if only you had any amount of patience whatsoever.”

He chuckled, “That’s what you’re here for.”

You climbed into the car, making sure to pull your dress out of the way before you shut the door. It was one of your favorites, and you’d rather it didn’t get too ruined. It was a dark blue sleeveless number, with tiny rhinestones speckled throughout it, that you thought looked very similar to stars. 

Stars that you could never quite see in the city. Even on the darkest of nights, there was too much light pollution. It was quite a shame, really. You loved the stars. 

You watched the city lights pass you by through the car window, which was never the same as being able to see the sky. You supposed that you couldn’t complain too much though. Ebott wasn’t a horrible place to live. Though, in all honesty, you didn’t have much to compare it to. You had always lived in Ebott.

That came with its perks, though. You knew the city like the back of your hand, and had connections to just about everyone worth having connections to. In fact, it hadn’t taken very long at all for you to become the one in charge of any and all social aspects of your father’s business. 

Those skills would be especially helpful tonight. You imagine that being able to put on a personality that wasn’t quite yours would be important if you wanted to keep up the illusion that you weren’t upset about all of this. 

As soon as the car stopped, you plastered a smile on your face. You could do this. You took a deep breath as the door was pulled open, and accepted the hand offered to you. You were unsurprised to see your father giving you an unsure smile. You looked forward and dropped his hand, making your way inside. 

The ballroom was filled with people and monsters of all shapes and sizes. They… weren’t hard to miss. Most, if not all monsters easily towered over humans. You had gotten over the initial intimidation that came with that rather quickly.

You took note of the way the groups remained pretty separated, with the exception of very few. Your smile faltered at that, but you shook it off and wandered inside. Instead of going to any particular crowd, you found yourself making your way to the side of the room. You wanted to be able to keep an eye on things until you felt like you had a decent lay out of the people you weren’t familiar with. 

You didn’t make it that far. About halfway through the room, an unfamiliar voice called out to you. 

“Excuse me, Miss!” You stopped in your tracks and turned back to face them. 

You were surprised to see a tall skeleton towering over you. You had to crane your neck to look up at him, though he seemed to notice that and slouched over. It didn’t help much. He gave you a small grin through a jaw full of crooked teeth. 

“I am very sorry to bother you! I just wanted to tell you that I like your dress very much! It looks just like starlight!” His voice was scratchy, but his words were sincere.

You smiled back, “Oh! Well thank you!” You decided to return the compliment, “I like your glasses! I think they look very dashing on you.”

He seemed a bit taken aback that you had said that. “You- uh, Thank you! I don’t think I’ve even had a human call me that before!”

That… that made you oddly sad. You had to fight the urge to clutch at your chest as his slightly melancholy expression turned back into a grin. You bit at your lip in thought. 

“I’m sorry to hear that,” you smiled, “but maybe you’ve just been talking to the wrong humans.” You reached a hand out to him, “It’s nice to meet you.”

He glanced between you and your hand a few times before taking it in his own and shaking it with an enthusiasm that you hadn’t expected, “Papyrus!” He told you.

Papyrus, huh? You looked down at his hand that was still wrapped around yours. As expected, his hand easily dwarfed your own. You sighed and looked back up at him. Your bleeding heart was going to get you killed one of these days.

“Well Papyrus, you wouldn’t happen to care for a dance, would you?” You gave him another smile. 

“Really?!” He cleared his throat, “I mean, of course you would like to dance with someone as great as I!” Oh no, he’s cute!

You nodded, “Of course!” 

You didn’t have the chance to say anything else before you were pulled to the center of the room with a sharp tug. Huh. Papyrus was stronger than he looked. 

Then you found a small hitch in your plan. Papyrus was at least a solid two feet taller than you, witch gave you a bit of pause. Papyrus seemed indifferent to it, and took both of your hands. Yeah, you supposed that would have to work.  Reaching up to rest a hand on his shoulder would be an awkward endeavor at best.

And work it did. You couldn’t help but grin as Papyrus lead you around the center of the room. His dancing was clumsy at best and awkward at worst, but you found that it just made the whole situation more endearing. You had to masterfully avoid getting your feet stomped on one or twice, but you didn’t mind. At some point, you started to enjoy yourself. It must have been the skeleton’s infectious grin, or maybe it was the way he was practically beaming at you. You got the sneaking suspicion that he didn’t get to opportunity to dance very often. 

He spun you, and you giggled with the enthusiastic movement. When he pulled you back, he began speaking, “So what brings you here tonight?”

You decided to dodge the question, “Well, I usually attend these kinds of things in lieu of my father. He’s terrible at social situations, I’m afraid.”

“He sounds like my brother.” Papyrus said, “Though my brother is here as well tonight. He couldn’t have gotten out of this one no matter how much he didn’t want to be here.” You could relate.

“I see.“ The next time he spun you, you took the opportunity to do a very quick scan of the people around you. “It seems a lot of us were dragged here,” you joked. 

After one more spin, he dropped your hands and smiled at you, “I suppose. I think that’s kind of sad, though.”

You shrugged, “I think the whole situation was very sudden.”

He sighed, “Maybe. But, it’s still a shame that so many people seem so down in the dumps.” He shook his head and quickly glanced around, “My brother is being a wallflower, as usual. I doubt he’s even tried to mingle!”

You chuckled and followed his line of vision as best as you could. Your smile dropped a bit as you noticed another skeleton monster leaning against the wall. He, like most monsters, towered over all of the humans in the room. A single red light from one of his eyes darted from face to face, and a scowl was set in his expression. That wasn’t why you were frowinging though. There was a hole in the side of his head. You got a headache just from glancing at it.

“Is he okay?” The question came before you could stop it, and while you had meant it in a concerned way, you knew that monsters could be more than a little touchy about… well, everything. 

“He’s just grumpy because he doesn’t want to be here,” Papyrus explained to you. That wasn’t exactly what you were asking about, but you were kind of glad the question seemed to go over his head. 

He looked away from you for a second in thought before turning back with a worried expression. “I’m so sorry Miss! I never even asked your name!”

You chuckled. What an odd monster. You prattled off your name. 

He froze immediately after. A small whine that sounded very reminiscent of a squeal escaped him before he dashed off without warning. What an odd monster indeed. You stared after his retreating form for a few seconds before shaking your head.

Your eyes wandered back to the other skeleton, who seemed to be glaring at the table that held all of the food. He really did look miserable. You sighed and made your way over to him. 

“What did those poor hors o‘ devours ever do to you?” You smiled at him even though he barely gave you a glance. 

After you stop there for a second, he looked at you once more. “Can I help you?”

“No, I don’t think so. I was just curious,” you shrugged.

He looked away, but to your surprise, he continued to talk to you. “That’s a pretty dangerous thing to be.”

“I guess. It’s a good thing that I’m only curious over your vendetta against the punch bowl instead of something more dire.” You found yourself absentmindedly scanning the crowd once more. 

“Something more dire, huh? Like what?” His voice was deep and gravely, and sounded vaguely like there was a point in time where it hadn’t been used a whole lot. He spoke somewhat slowly as well, which you knew to mean he was choosing his words carefully.

You thought for a second before coming up with something mundane, “Are there actually parallel universes?”

He finally looked over at you in surprise. The monster took a second to look you over before a small chuckle came from him, “The better question is: is there a parallel universe where I don’t have to be at this dumb thing?”

Your smile turned into a grin, “Can I trade places with that version of me?”

His mouth twitch up into a smirk before he looked back at the table, “Things like this are stupid and pointless. ‘Specially if there are humans involved.” He crossed his arms, “You guys waste a lot of your resources.”

You weren’t sure if he meant any offense by that, but you chose to believe that he didn’t. “Yeah. Humans are the worst,” you agreed with a small smile. 

He gave you an odd look as you said that. The monster took a second just to stare at you. The light in his eye seemed to bore into the longer the silence stretched on. Usually, you would be uncomfortable with the amount of staring that was going on, but for some reason, you found that it almost seemed normal with him. It felt like he was observing you. It was like you were some kind of puzzle that he needed to solve. 

You gave him a small smile. He tilted his head at you, though his expression didn’t change. He looked as though he lost himself in thought for a second before he shook his head and looked away. 

“I didn’t even want to be here, anyways. This whole thing is stupid. I never asked to be married off, but the old man decided that it would be the best plan or whatever,” He mumbled, and you had a feeling that he hadn’t entirely meant it for you.

You blinked up at him in surprise. He was- you were… oh. Well, at least you could understand where he was coming from. 

You frowned and crossed your arms. “Well, if it makes you feel any better, I don’t particularly want to be married either. No offense or anything, I’m sure you’re a great guy, but I don’t really know you.” 

He froze and slowly looked over to you once more, “You-“ he cut himself off.

You offered him a hand and gave him your name, “I wish we could have met under better circumstances.” 

He didn’t take your hand. You smiled at him despite that, but you did drop your hand. You let out a small sigh and shook your head. He was going to make this difficult, wasn’t he?

He narrowed his sockets at you, “Sans.” 

You felt your shoulders drop in relief, “Okay. Thank you, Sans.”

“What’re you thanking me for?” You notice that his fingers began tapping against his leg. You wondered briefly if that was a nervous habit, or if it was just something to keep him busy. 

“It seems that neither of us really wants anything to do with this. You could have completely ignored me, but you didn’t. So, thank you for not making this as miserable as it could have been.” You shook your head and backpedaled, “I mean, that’s not to say that I’m miserable! I didn’t mean it like that, I just meant-“

“I know what you meant,” he deadpanned, but you could have sworn that you noticed a spark of amusement in his gaze.

“Right. Sorry for rambling,” you sheepishly rubbed at your arm.

He hummed and looked you over once more, “You are… not what I was expecting.”

“No? And what were you expecting?” You raised a brow in question. 

He grunted at you, but other than that, didn’t answer your question. You knew when your questions weren’t going to be answered, and you could tell that this was going to be one of these times. 

Okay, maybe a change of subject would be your best bet here. “Papyrus is your brother, yes?”

His attention snapped to you once more, “Why?” The light in his eye flickered. You had to fight back a flinch.

Showing that you had any ounce of fear towards him would not help your case. But, you supposed that was just the life you lead. Weakness is bad. If you’re weak, this city would chew you up and spit you out. No, there was no room for fear. 

“Woah there. I was just trying to make conversation. He already pointed you out to me, anyways.” You could feel the sudden hostility in his gaze, and with that came the need to calm him, “He’s a sweetheart.” You glanced in the direction he had run off in, suddenly understanding his quick retreat. 

“Maybe,” he answered vaguely. 

You chuckled, “He’s your younger brother, right?” When Sans nodded, you continued, “I figured. Not because of any reason in particular, though. You just kind of strike me as an older brother.”

“That sounds like you’re speaking from experience,” he pointed out.

“No. I always wanted sibling when I was growing up, though,” you smiled, “I didn’t get any, but I guess that’s okay. There were a couple of guys who ended up being like brothers to me, even though that’s not really the same.”

“You overshare,” Sans seemed to take in the information anyways. 

“Not usually,” you glanced around the room once more, “If you’re going to be stuck with me, I’d rather that we get along. You seem like the kind of person that gets along better with people he knows more about.”

He stared at you once more before a soft chuckle escaped him, “You aren’t wrong, though it’s a pretty big assumption that I ’get along’ with anybody.”

You shrugged, “Worth a shot to try, at least.”

“Good luck.” You couldn’t tell if he was being sincere or not. He was definitely hard to gauge. You knew that this would be difficult for you from the very beginning, but damn if he wasn't going to be the bane of your existence while you tried to figure him out. You knew from the look he was giving you that he was trying to do the exact same thing. 

There was no way you could fault him for doing so. You knew that you really didn’t have any ulterior motives other than you were asked to do this by our father, but Sans didn’t know that. Sans didn’t know  _ you. _ It only made sense that he was weary of you. 

It wasn’t often that people in your business were given the benefit of the doubt. You understood perfectly why that was, and yet, you had always found yourself doing just that. Now, you weren’t nieve. In fact, you were very far from it. Growing up in the life that you did, you could spot bad intentions from a mile away. You were just the kind of person that always wanted to give everyone a chance. 

You didn’t let that get in the way of what you needed to do, though. 

You tapped your fingers in thought, your eyes quickly scanning over the crowd of people. You saw a few familiar faces, though you had never interacted with them too much. They were all people who worked for your father, and most of them had wives or girlfriends or  _ whatever they might have been _ hanging off of their arms. The rest of the room consisted of monsters. 

It never stopped surprising you how different monsters could be from one another. You could pick out a few different large dog monsters with some kind of gnarly looking armor, and even gnarlier teeth. There was a few monsters that you wouldn’t even know where to begin to describe them, any you were pretty sure that you had seen a man made of literal fire weaving in and out of the crowd. It was kind of jarring to see them all in one place. 

You briefly wondered if it was the same for them. Sure, humans were a lot smaller, but their numbers were much, much greater. Though, you did have to admit that the human numbers in your city had fallen particularly low since the monsters had emerged. You fought back a grimace at the thought. 

“What do you think the chances are of being able to sneak out without being noticed?” You asked the skeleton monster. 

He glanced over at you once more, a single red iris focused on you, “now that I know who you are, I’d say zero.”

“You’re right. I suppose that they’ll be on the lookout for a runaway bride, huh?” 

“Knowing my old man, I’m bet money on it,” his gaze shifted once more to the crowd, though this time you could see his attention very obviously shift between the different monsters in the room.

Maybe trying to sneak out wasn’t the best idea. Running out on a mob family was never,  _ ever  _ a good idea. Not that you were actually planning on doing that anyways. Sans wasn’t terrible company, at least. 

“Yeah, that’s a bet that I’d have to skip. I don’t think I’m willing to lose the money on that one.” You ended that with a small chuckle. “I’m not much of a gambler, anyways.”

He just hummed at you in response. Right. Good. You got the sneaking suspicion that you’d be doing most of the talking with him. Well, for now at least. Hopefully you’d eventually get a half-decent conversationalist out of him. Hopefully.

If not, well, this was going to be a long process. 

**Notes for the Chapter:**

> Welp, here we go! 
> 
> Just a fair warning, I have absolutely no clue where I’m gong with this story in particular. That being said, updates will most likely be sporadic and slow, but the chapter will proably be longer! Maybe expect one a month or so!

**Author's Note:**

> [Stop by my Tumblr and say hello!](https://lost-immortality.tumblr.com)


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